Avery Anna brought her “Girl of Constant Sorrow Tour” during its last week to the Rave Eagles Club in Milwaukee back in May. Before this concert, the UWM Post spoke exclusively with Anna about her music, the tour and the ACM Awards.
Not long after being named the Academy of Country Music Awards’ new female artist of the year, the 22-year-old took the stage at the Eagles Ballroom. Fans showed up dressed in their best western-inspired attire, which of course included cowboy/cowgirl boots and hats.
“The reason I called it the ‘Girl of Constant Sorrow Tour’ is because my life has kind of changed in the blink of an eye. It’s a lot of whiplash going from driving around this country in my car, to then having a full crew and the bus to sleep in,” Anna said during the concert.
The Opening
Fellow 22-year-old artist Ashley Anne took the stage before Anna to deliver an appropriate opening performance that matched Anna’s sound and vibe.
The fans anxiously shuffled around the venue and bought merch, sang along to the pre-show playlist and wrote letters to Anna. The playlist represented Anna’s versatile music taste with country, rock, pop and more genres of songs.
One song that everyone in the crowd sang along to was Toby Keith’s “Red, White, and Blue (The Angry American).” With the lyrics “‘Cause we’ll put a boot in your a**, it’s the American way,” getting a loud, echoing uproar from the audience.
A tradition that has developed at Anna’s concerts is fans writing letters to her about something negative that they need to let go of or sharing something positive in their life.
I even grabbed one of the pieces of paper that had a purple butterfly on it, her signature logo, and wrote a letter about my excitement to see her perform.
The crowd at an Avery Anna concert has everyone from young girls to adult women who bring their boyfriends along. There is diversity in age and personality, just like Anna’s musical taste.
Finally, with heavy anticipation, Anna took the stage and began singing her song “Blame It On My Broken Heart.”
After opening with that song and then following it with “Mr. Predictable” and “Blonde,” Anna checked in with the crowd, specifically the men in the room.
“I don’t know, guys, are you okay? That was three in a row of just,” Anna says and gestures to the crowd with a smirk, referring to all the first three songs being about men being bad in relationships. The crowd laughs.
“I feel like it’s a pretty green flag if you’re a guy and you’re at an Avery Anna show,” Anna said.
The guys in the crowd erupt with loud applause and cheers as Anna begins to sing her cover of “Man I Need” by Olivia Dean.
After the cover, Anna addresses the men in the crowd again. “As much as we like to sing about it, we are not truly man-haters here. We love our men, but those boys though.”
This led into the lyric of her next song, “Life Ain’t Like The Rodeo,” which is “Boys in the Bible Belt ain’t that holy.”
The Concert Experience
Avery Anna knows how to put on an electric and lively performance, as well as actively engaging with the audience.
“I hope you know that whatever you are dealing with right now in your lives, whatever’s weighing down on your shoulders, this is a place where you can truly let it go and let the music take it away,” Anna told the audience at the Rave.
My favorite parts of the concert are when she gets vulnerable with the crowd, and in turn, the crowd lets their guard down and feels the emotions together.
Equally engaging are the parts of the show when Anna turns it into a full-blown rock concert.
“I hope you weren’t looking to have a good time tonight. I hope you came to cry. If not, the bar is located in the back,” Anna joked with the crowd during the show about the sad music in her catalogue.
Everyone in the audience sang and tapped their feet along to not only the excellent covers, but also Anna’s enthralling originals. I felt that she was coming off a high of winning her ACM, and you could feel the confidence she had in her ability.
As Anna has talked about in interviews and her personal TED Talk, she creates an experience where everyone can feel these heavy emotions together and share in that moment.
Special moments from the concert include Anna bringing out the opening act, Ashley Anne, to duet on “Love Story” and the ending performance of “Indigo.”
The Background of Avery Anna’s Stardom
After going viral, Anna signed to Warner Music Nashville, for whom she has released two full-length albums, “Breakup Over Breakfast” and “Let Go Letters,” and two EPs: “Mood Swings” and, most recently, “forgive, forget.”
Anna is an exciting up-and-coming singer/songwriter from Arizona who has been making waves online and in Nashville. She reached the Top 10 on Billboard’s Hot Country Songs chart with Sam Barber for their Platinum-certified, viral duet “Indigo,” which they performed together on “The Kelly Clarkson Show.”
“Let Go Letters,” her sophomore album, was named on the list of top 50 albums of 2025 by Rolling Stone. This album was inspired by the letters that she receives from fans at her concerts.
The album was a deeply personal record for both her and her fans, which showed off a truly vulnerable and relatable side to the young artist.
Humble Beginnings & Virality
“Not even a year ago, we were in a van. It smelled like dog pee, and I was like, ‘Hey, you guys, isn’t it so great that nothing is broken. Today, nothing’s gone wrong. How blessed is this day?’ Anna said to the crowd. “Like a minute later, our trailer broke, and we were broken down on the side of the road.”
Anna would then go on to film a video of her singing an unreleased song while the trailer was getting fixed. The video would go on to become viral, and she released the song.
“Literally and figuratively, when I’ve been broken down on the side of the road in my life, music has been that one thing that has really saved me,” Anna said.
With her quick rise, it’s no telling how much longer her fanbase will be able to fit in medium-sized venues, like the one she performed in at the Rave in Milwaukee.
Recent female country-influenced artists, such as Megan Moroney and Ella Langley, have been popping off, and Anna might be the next one to explode in popularity.
The Concert Setlist
Anna’s setlist included a mix of her original songs from a variety of her projects, as well as some fan-favorite covers. The variety of music was impressive and kept me on my toes as to what to expect would come next.
Understanding the energy of a show is important, and Anna delivered on having somber moments as well as high-energy moments sprinkled evenly throughout the performance.
At any of her concerts, the attendee can expect to go from rocking out one minute to crying it out the next minute. Anna’s songs and stage presence brought everyone on an emotional roller coaster throughout the night.
The Songs
- “Blame It On My Broken Heart”
- “Mr. Predictable”
- “Blonde”
- “Man I Need” – Olivia Dean cover
- “Life Ain’t Like The Radio”
- “Blood Runs Thicker”
- “Giddy Up!” – collaboration with Maggie Antone
- “lonestar alone”
- “it’s just rainin'”
- “No More Tears” – Ozzy Osbourne cover
- “Girl of Constant Sorrow”
- “forgive, forget.”
- “Love Story” – Taylor Swift cover
- “Ice Ice Baby” – Vanilla Ice cover
- “Party In The U.S.A.” – Miley Cyrus cover
- “vanilla”
- “GRAVE”
- “Man Downstairs”
- “Narcissist”
- “Fear in God” – collaboration with Sam Barber
- “Make It Look Easy”
- “Indigo” – collaboration with Sam Barber
Meeting with Fans After Concert:
